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Also known as: 327-97-9, 3-o-caffeoylquinic acid, Heriguard, 3-(3,4-dihydroxycinnamoyl)quinic acid, 3-caffeoylquinic acid, Chlorogenate

Molecular Formula

C₁₆H₁₈O₉

Molecular Weight

354.31 g/mol

InChI Key

CWVRJTMFETXNAD-JUHZACGLSA-N

FDA UNII

318ADP12RI

A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68).

1 2D Structure

Chlorogenic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid

2.1.2 InChI

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

2.1.3 InChI Key

CWVRJTMFETXNAD-JUHZACGLSA-N

2.1.4 Canonical SMILES

C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O

2.1.5 Isomeric SMILES

C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

318ADP12RI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3 Caffeoylquinic Acid

2. 3-caffeoylquinic Acid

3. Acid, 3-caffeoylquinic

4. Acid, Chlorogenic

2.3.2 Depositor-Supplied Synonyms

1. 327-97-9

2. 3-o-caffeoylquinic Acid

3. Heriguard

4. 3-(3,4-dihydroxycinnamoyl)quinic Acid

5. 3-caffeoylquinic Acid

6. Chlorogenate

7. Hlorogenic Acid

8. Cp Chlorogenic Acid

9. Nsc-407296

10. Caffeoyl Quinic Acid

11. 5-cqa

12. (+)-chlorogenic Acid

13. Chlorogenic Acid [mi]

14. 5-o-(3,4-dihydroxycinnamoyl)-l-quinic Acid

15. Trans-chlorogenic Acid

16. Caffetannic Acid

17. Trans-caffeic Acid 5-o-d-quinate

18. Chlorogenic Acid [who-dd]

19. Cis-chlorogenic Acid

20. Nsc 70861

21. Nsc-70861

22. (1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

23. Nsc 407296

24. Trans-5-o-caffeoylquinic Acid

25. 318adp12ri

26. Chembl284616

27. 202650-88-2

28. Chebi:16112

29. Cyclohexanecarboxylic Acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1-alpha,3-beta,4-alpha,5-alpha))-

30. Chlorogenic Acid (constituent Of St. John's Wort) [dsc]

31. Mfcd00003862

32. 3-o-(3,4-dihydroxycinnamoyl)-d-quinic Acid

33. (1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

34. Chlorogenic Acid (constituent Of Echinacea Angustifolia Root, Echinacea Pallida Root, Echinacea Purpurea Root And Echinacea Purpurea Aerial Parts) [dsc]

35. Cyclohexanecarboxylic Acid, 3-(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

36. Cyclohexanecarboxylic Acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

37. Cyclohexanecarboxylic Acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

38. Chlorogenicacid

39. Caffeoylquinic Acid

40. 1,3,4,5-tetrahydroxycyclohexanecarboxylic Acid 3-(3,4-dihydroxycinnamate)

41. 3-o-caffeoyl-d-quinic Acid

42. 1,3,4,5-tetrahydroxycyclohexanecarboxylic Acid 3-(3,4-dihydroxycinnamate

43. 3-caffeoylquinate

44. 5-caffeoylquinic Acid

45. 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic Acid

46. 5-caffeoyl Quinic Acid

47. (1s,3r,4r,5r)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

48. [1s-(1alpha,3beta,4alpha,5alpha)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid

49. [1s-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid

50. Cyclohexanecarboxylic Acid, 3-[[(2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

51. Cyclohexanecarboxylic Acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, [1s-(1alpha,3beta,4alpha,5alpha)]-

52. Ccris 1400

53. Einecs 206-325-6

54. 3-trans-caffeoylquinic Acid

55. Unii-318adp12ri

56. Hlorogenate

57. Helianthic Acid

58. Igasuric Acid

59. Nsc70861

60. Chlorogenic-acid

61. Nsc407296

62. Caffeylquinic Acid

63. 3-(3,4-dihydroxycinnamoyl)quinate

64. Prestwick_112

65. (e)-chlorogenic Acid

66. Hoodia Chinese Extract

67. Chlorogenic Acid, Chiral

68. Chlorogenic Acid (8ci)

69. Prestwick2_000427

70. Prestwick3_000427

71. Spectrum5_000733

72. Bmse000387

73. Quinic Acid, 5-caffeoyl-

74. Schembl19466

75. Bspbio_000414

76. Bspbio_003353

77. Spectrum210800

78. Mls002153805

79. Bidd:er0453

80. Bpbio1_000456

81. Quinic Acid, 3-caffeoyl-, E-

82. Acon1_000581

83. Chebi:95271

84. Chlorogenic Acid [usp-rs]

85. Bdbm513080

86. Dtxsid101318952

87. Hms1569e16

88. Hms1923c11

89. Hms2096e16

90. Hms2235f03

91. Hms3649e06

92. Act03375

93. Albb-030169

94. Cga

95. Hy-n0055

96. Zinc2138728

97. Bdbm50327036

98. Ccg-38471

99. S2280

100. Akos015955866

101. Ac-6032

102. Chlorogenic Acid, >=95% (titration)

103. Cs-3766

104. Db12029

105. Sdccgmls-0066467.p001

106. Ncgc00168941-01

107. Ncgc00168941-02

108. Ncgc00168941-03

109. (1s,3r,4r,5r)-3-(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

110. (1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

111. As-12284

112. Smr000857273

113. Chlorogenic Acid 100 Microg/ml In Methanol

114. Chlorogenic Acid 1000 Microg/ml In Acetone

115. Chlorogenic Acid 10 Microg/ml In Acetonitrile

116. C00852

117. F16266

118. 327c979

119. Q421964

120. Sr-01000841185

121. Sr-01000946600

122. D54cae3d-cdda-455d-a28e-77fc9efe4a43

123. Sr-01000841185-4

124. Sr-01000946600-1

125. Brd-k47114202-001-06-2

126. 32cf6d13-8f08-485f-b79e-f8a6ac318e07

127. Chlorogenic Acid, Primary Pharmaceutical Reference Standard

128. Chlorogenic Acid, European Pharmacopoeia (ep) Reference Standard

129. Chlorogenic Acid, United States Pharmacopeia (usp) Reference Standard

130. 3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

131. 3-[3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

132. (1r,3s,4s,5s)-3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

133. (1s,3r,4r,5r)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylicacid

134. (1s,3r,4r,5r)-3-(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

135. (1s,3r,4r,5r)-3-((e)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

136. (1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

137. (1s,3r,4r,5r)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid

138. (1s,3r,4r,5r,e)-3-(3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

139. Cyclohexanecarboxylic Acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1-.alpha.,3-.beta.,4-.alpha.,5-.alpha.))-

140. Cyclohexanecarboxylic Acid,3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1s,3r,4r,5r)-

141. Edit(1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₈O₉
Molecular Weight	354.31 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	354.09508215 g/mol
Monoisotopic Mass	354.09508215 g/mol
Topological Polar Surface Area	165 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	534
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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